EP1740550A1 - Sulphur-linked imidazole compounds for the treament of hiv - Google Patents

Info

Publication number

EP1740550A1

EP1740550A1 EP05728902A EP05728902A EP1740550A1 EP 1740550 A1 EP1740550 A1 EP 1740550A1 EP 05728902 A EP05728902 A EP 05728902A EP 05728902 A EP05728902 A EP 05728902A EP 1740550 A1 EP1740550 A1 EP 1740550A1

Authority

EP

European Patent Office

Prior art keywords

compound

formula

preparation

ethyl

imidazol

Prior art date

2004-04-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

• Espacenet
• EPO GPI
• EP Register
• Global Dossier
• Discuss

• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 2
• 239000005864 Sulphur Substances 0.000 title description 2
• 150000002460 imidazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 355
• 238000002360 preparation method Methods 0.000 claims abstract description 166
• 238000000034 method Methods 0.000 claims abstract description 55
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 239000012453 solvate Substances 0.000 claims abstract description 42
• 102100034343 Integrase Human genes 0.000 claims abstract description 7
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 claims abstract description 7
• 230000008569 process Effects 0.000 claims abstract description 7
• 238000006243 chemical reaction Methods 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 26
• -1 pyridyl N-oxide Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 229940124597 therapeutic agent Drugs 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 10
• 208000030507 AIDS Diseases 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 206010038997 Retroviral infections Diseases 0.000 claims description 7
• 230000029936 alkylation Effects 0.000 claims description 7
• 238000005804 alkylation reaction Methods 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• LSWRYEAIHSAKRL-UHFFFAOYSA-N 5-[2-(2-hydroxyethyl)-3-methyl-5-propan-2-ylimidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound N1=C(CCO)N(C)C(SC=2C=C(C=C(C=2)C#N)C#N)=C1C(C)C LSWRYEAIHSAKRL-UHFFFAOYSA-N 0.000 claims 1
• LLTPREXBESSGAL-UHFFFAOYSA-N 5-[2-(hydroxymethyl)-5-propan-2-yl-3-(pyridin-4-ylmethyl)imidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound C=1C(C#N)=CC(C#N)=CC=1SC1=C(C(C)C)N=C(CO)N1CC1=CC=NC=C1 LLTPREXBESSGAL-UHFFFAOYSA-N 0.000 claims 1
• CHNWBWOWXMJJFM-UHFFFAOYSA-N 5-[3,5-diethyl-2-(2-hydroxyethyl)imidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound N1=C(CCO)N(CC)C(SC=2C=C(C=C(C=2)C#N)C#N)=C1CC CHNWBWOWXMJJFM-UHFFFAOYSA-N 0.000 claims 1
• WBJWSLGXANVNBH-UHFFFAOYSA-N 5-[3-ethyl-2-(2-hydroxyethyl)-5-(trifluoromethyl)imidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound CCN1C(CCO)=NC(C(F)(F)F)=C1SC1=CC(C#N)=CC(C#N)=C1 WBJWSLGXANVNBH-UHFFFAOYSA-N 0.000 claims 1
• JGMYQAJFRLHDSO-UHFFFAOYSA-N 5-[3-ethyl-2-(2-hydroxyethyl)-5-propan-2-ylimidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound CCN1C(CCO)=NC(C(C)C)=C1SC1=CC(C#N)=CC(C#N)=C1 JGMYQAJFRLHDSO-UHFFFAOYSA-N 0.000 claims 1
• DBLGRPUVURZRHW-UHFFFAOYSA-N 5-[5-cyclopropyl-3-ethyl-2-(2-hydroxyethyl)imidazol-4-yl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound C=1C(C#N)=CC(C#N)=CC=1SC=1N(CC)C(CCO)=NC=1C1CC1 DBLGRPUVURZRHW-UHFFFAOYSA-N 0.000 claims 1
• CNYXMYZEAXGHCS-UHFFFAOYSA-N [4-cyclopropyl-5-(3,5-dicyanophenyl)sulfanyl-1-ethylimidazol-2-yl]methyl carbamate Chemical compound C=1C(C#N)=CC(C#N)=CC=1SC=1N(CC)C(COC(N)=O)=NC=1C1CC1 CNYXMYZEAXGHCS-UHFFFAOYSA-N 0.000 claims 1
• FMWRSYGBWVGJSK-UHFFFAOYSA-N [5-(3,5-dicyanophenyl)sulfanyl-1,4-diethylimidazol-2-yl]methyl carbamate Chemical compound N1=C(COC(N)=O)N(CC)C(SC=2C=C(C=C(C=2)C#N)C#N)=C1CC FMWRSYGBWVGJSK-UHFFFAOYSA-N 0.000 claims 1
• IMJPPGNSLQXYJM-UHFFFAOYSA-N [5-(3,5-dicyanophenyl)sulfanyl-1-ethyl-4-(trifluoromethyl)imidazol-2-yl]methyl carbamate Chemical compound CCN1C(COC(N)=O)=NC(C(F)(F)F)=C1SC1=CC(C#N)=CC(C#N)=C1 IMJPPGNSLQXYJM-UHFFFAOYSA-N 0.000 claims 1
• HELDRUHJBNOPHC-UHFFFAOYSA-N [5-(3,5-dicyanophenyl)sulfanyl-1-ethyl-4-propan-2-ylimidazol-2-yl]methyl carbamate Chemical compound CCN1C(COC(N)=O)=NC(C(C)C)=C1SC1=CC(C#N)=CC(C#N)=C1 HELDRUHJBNOPHC-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 129
• 239000003112 inhibitor Substances 0.000 abstract description 9
• 239000000543 intermediate Substances 0.000 abstract description 6
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical class N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 240
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
• 239000000243 solution Substances 0.000 description 122
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 68
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 60
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 53
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
• 239000007787 solid Substances 0.000 description 51
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
• 239000010410 layer Substances 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• 239000000741 silica gel Substances 0.000 description 37
• 229910002027 silica gel Inorganic materials 0.000 description 37
• 239000012267 brine Substances 0.000 description 35
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 34
• 235000019341 magnesium sulphate Nutrition 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• 238000009472 formulation Methods 0.000 description 29
• 230000002829 reductive effect Effects 0.000 description 28
• 239000002904 solvent Substances 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 238000004440 column chromatography Methods 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 239000003921 oil Substances 0.000 description 22
• 235000019198 oils Nutrition 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 21
• 229910021529 ammonia Inorganic materials 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
• 241000725303 Human immunodeficiency virus Species 0.000 description 17
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• 239000003826 tablet Substances 0.000 description 16
• 239000002585 base Substances 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 13
• 238000004587 chromatography analysis Methods 0.000 description 13
• 229910052740 iodine Inorganic materials 0.000 description 13
• 239000011630 iodine Substances 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 12
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 238000010828 elution Methods 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 239000002552 dosage form Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
• 238000002844 melting Methods 0.000 description 9
• 230000008018 melting Effects 0.000 description 9
• AYEIJQRLYWJQHC-UHFFFAOYSA-N methylsulfanylmethane;trichloroborane Chemical compound CSC.ClB(Cl)Cl AYEIJQRLYWJQHC-UHFFFAOYSA-N 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
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• 239000006260 foam Substances 0.000 description 8
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
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• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 7
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• 238000001914 filtration Methods 0.000 description 6
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